Water → HCID 18397081, compound

HRID 369039Notes

Reaction equation

HRID 369039 reaction equation
[F:1][CH:2](P(=O)(C1C=CC=CC=1)C1C=CC=CC=1)[F:3].C(NC(C)C)(C)C.[Li].[O:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1[O:32][C:33]1[CH:50]=[CH:49][C:48]2[C@@H:47]3[C@H:38]([C@H:39]4[C@@:43]([CH2:45][CH2:46]3)([CH3:44])[C:42](=O)[CH2:41][CH2:40]4)[CH2:37][CH2:36][C:35]=2[CH:34]=1.O>O1CCCC1>[F:1][C:2]([F:3])=[C:42]1[CH2:41][CH2:40][C@H:39]2[C@H:38]3[C@H:47]([CH2:46][CH2:45][C@:43]12[CH3:44])[C:48]1[CH:49]=[CH:50][C:33]([O:32][CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31][O:26]2)=[CH:34][C:35]=1[CH2:36][CH2:37]3

Participants

6

Reactant 4

HCID 962WaterHCID 10405885Estrone THP EtherHCID 15635908(Difluoromethyl)(oxo)diphenyl-lambda~5~-phosphaneHCID 45051747Lithium diisopropylamine

Product 1

HCID 18397081HCID 18397081, compoundYield 111.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

757 mg of difluoromethyl-diphenyl-phosphine-oxide (M. L. Edwards et al. Tetrahedron Letters p. 5571, 1990) in 38 ml of tetrahydrofuran is slowly mixed with 1.5 ml of a 2 M lithium diisopropylamine solution at -50° C., stirred for 1 hour, and mixed with a solution of 1.06 g of 3-tetrahydropyranyloxy-estra-1,3,5 (10)-trien-17-one in 11 ml of tetrahydrofuran. It is stirred for 15 minutes at -50° C., allowed to come to room temperature and stirred for 3.5 hours at a bath temperature of 80° C. For working-up, it is added to water, extracted three times with ethyl acetate, the organic phases are washed neutral with saturated sodium chloride solution, dried on sodium sulfate and evaporated to dryness in a vacuum. 1.3 g of crude 17-difluoromethylene-3-(tetrahydro-pyran-2-yl-oxy)-estra-1,3,5(10)-triene is obtained.

Workup

  1. stirringIt is stirred for 15 minutes at -50° C.
  2. customto come to room temperature
  3. stirringstirred for 3.5 hours at a bath temperature of 80° C
  4. extractionextracted three times with ethyl acetate
  5. washthe organic phases are washed neutral with saturated sodium chloride solution
  6. customdried on sodium sulfate
  7. customevaporated to dryness in a vacuum

Sources & evidence

ORD record
ord-5444675556844f9a9a78cd67096aaec8
Source dataset
uspto-grants-2000_10
Patent number
US06136800

Reaction notes

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